The Bet - Chapter 61(Wednesday – week 9 Part 4 of 8)

The Bet

By Karen Singer

Chapter 61(Wednesday – week 9 Part 4 of 8)

     Chad had a problem.  Mel had been in the office much longer than he thought she would.  The crazy secretary had finally stopped staring at him… at least not quite so constantly… and she had even finally answered the phone.  But his problem was that a few minutes ago, he had felt a bit of pee leaking out from his diaper.  It was only a tiny bit, not enough to rush down his leg yet, but he could still feel it.  If Mel didn’t get out of there soon, he was going to have a big problem on his hands because then it would be rushing down his leg.  Why was it that some of his diapers could be so stubborn when it came to leaking… and now, of all times, this one wasn’t!

     The door finally opened, and Mel walked out… looking happier than she had when she walked in.  “Everything okay out here?” she asked offhandedly. 

     Chad curtseyed, much to the secretary’s amusement again, and removed the pacifier from his mouth.  “Not quite,” he replied softly as Mel was about to walk right past him.  He put the pacifier back in his mouth and curtseyed again.

     Mel stopped in her tracks.  “What’s the problem?” she asked with some concern.

     Curtsey… pacifier.  “I’m leaking,” Chad replied very softly.  Pacifier… curtsey.

      “What?” Mel replied.  He had spoken so softly she hadn’t heard him.

     Chad sighed, then curtseyed and removed his pacifier again.  “I’m leaking,” he said a little louder before plugging his mouth and curtseying again.

      “You’re leaking?” Mel asked.  She smiled.  “Pull your dress up.  Let me see.”

     In full view of the secretary behind the desk, Chad grabbed the front of all his skirts as best as he could.  The tiny purse he had to hold in his hand didn’t help matters, but he was still able to grab all his skirts and pull them up… completely exposing the soggy diaper he was wearing underneath.

     Mel took the time to stare at his soaked diaper for a few moments, knowing that it would be terribly humiliating for Sissy to expose it that way.  “Very good, Sissy,” she said.  “Keep those skirts pulled up just like that till we get back to the car.  I’m sure everyone will want to see how wet your diaper is.”  With that, she purposely strode back down the hall… back toward the elevator.  She didn’t have to look at Harry’s secretary to know she was probably having a fit.  She would now have even more to remember this little visit.

     Chad had no choice but to continue to hold his skirts up high as he now followed Mel back to the elevator again.  He felt horribly embarrassed, but at least they were now heading back out to the car and it would all soon be over.  He was glad to be able to turn his back to everyone as they reached the elevator and Mel pushed the button to call for it again.

     Once again Mel had to wait for the slow elevator.  She looked over at Sissy standing next to her, his face turned embarrassedly down toward the floor, his skirts still held high exposing the front of his overly soggy diaper.  “Turn around,” she told him.  “Show everyone behind us how wet your diaper is.”

     Chad wanted to die!  Slowly, he turned all the way around so that everyone in the desks behind him would be able to see.  But his eyes never left the floor. 

     Knowing how embarrassing it would be for him, she said, “Walk around, Sissy.  Go show everyone up close how wet you are right now.”

     Chad couldn’t believe it!  How could she possibly…  He heard the elevator ding as it arrived and the door opened.  He turned toward it instead.

      “It can wait, Sissy,” Mel said sternly.  “I’m sure all these nice people would like to see how wet that diaper you’re wearing is before we leave.”

     Chad not only felt himself peeing again in humiliation, he now felt that pee starting to run quickly down his leg!  Slowly and embarrassedly, he approached the woman at the first desk.  He didn’t stop, he just slowly walked past her towards the desk behind her.

      “Oh my God!” the woman exclaimed.  “He’s not only soaked, he’s leaking!”

     One by one, every person at the desks got a good view of Sissy’s soggy leaking diaper.  He had never felt so ashamed in his life as he walked slowly around through all the desks.  He was very grateful to finally get back to the elevator where Mel was now holding the door open.  He didn’t pause in the least as he entered the thing and stood facing the back wall. 

      “Turn around Sissy so they can all see you,” Mel ordered, still holding the door wide open.

     Feeling totally ashamed, Chad slowly turned back around to face everyone again. 

     With a big smile on her face, Mel gave a quick wave to everyone watching and let the elevator door close.  Chad just continued to hold his skirts up and stare at the elevator floor.  And all too soon, the door opened again and Mel stepped out.  Part of Chad wanted to stay right where he was… somewhat hidden. But that wouldn’t work very well.  He followed Mel back out into the lobby, where several people paused to stare at the two as they headed for the doors. 

     Chad was ever so glad when they reached Mel’s car again, even though she wouldn’t let him get in.  Right there in the parking lot, she removed his soggy diaper and replaced it with a fresh one.  As she did it, Chad didn’t want to look up to see if anyone was watching from the upper floor windows.  Enough people had seen him as it was.  At least he had a dry diaper on again.

      “An hour and forty-five,” Mel said as she finished taping his new diaper in place.  “You can lower your dress now and wrap up that old diaper.”  She left him standing there next to her car as she went around to the driver’s side and got in. 

     Chad quickly took care of his old diaper and got in the car as well.  He was so glad to get somewhat out of sight.  He wasn’t as glad when Mel held out his baby bottle for him to take and start drinking again. 

     Mel started the car and backed out of the parking place.  “Well,” she said as she put the car in gear to go forward, “that was interesting.”

     Ray was feeling a bit woozy and tired again, but this time it wasn’t because of alcohol.  The tiger had been out for blood last night – his blood!  They had made love for hours… if you could call that making love.  And not once did she let him cum!  Not once!  It was more like she was punishing him for what he had done with Mel.  And the more he thought about it, the more he was sure that’s exactly what had gone on.  But it had certainly been lots of fun.  Mostly.  And today he was certainly feeling the effects from it. 

     And just before they had finally parted last night, she had told him that she expected him to take her out for a very expensive dinner Saturday night and maybe some dancing as well.  She had also made a point to tell him not to call her before then, just pick her up Saturday night.  She had been awfully demanding… but at least she was still speaking to him.  So she was now the first and only date he had set up for the entire week!  And oddly, he had no inclination to ask anyone else out before that.  He put it down to being so worn out from last night.

     But thinking about Gloria made him think about Mel as well… the rich one!  He had certainly blown that one!  Damn it!  And naturally, thinking about Mel, made him remember Chad… or Sissy.  What kind of bet had they entered that would have that kind of consequences?  Geez it had to be really something for Chad to go through what he was.  Major consequences! 

     He figured that since Mel was a lawyer, Chad had to be afraid of some kind of legal backing behind her – as unlikely as that sounded.  And the one and only thing that he could think of that might account for Chad having to put up with being dressed as a woman… and be her damn maid… was money!  Big money!  Major money! 

     Chad had just gotten divorced.  Had Chad been desperate enough to take a risk on something in order to get a big wad of cash?  No matter how he looked at it, it was still the only thing he could think of.  It had to be the reason!  But… he just wasn’t sure!

     Chad was out for the rest of the week so he couldn’t easily ask him.  Robin didn’t seem to know either.  He would have asked Derek again, but yesterday Derek had spent all day working at the job site and he was supposed to be there all day again today.  In fact, Derek was scheduled to be there all week.  So asking Derek was out.  So who could he ask?  Chad was out.  Derek was out.  He wasn’t about to ask Gloria about it, that was for sure!  And of course he certainly wasn’t going to phone Mel to ask her either.  And Chad’s coworker Robin didn’t know either… or she had said she didn’t know much.  But “much” meant that she probably did know some things.  But what?

     He checked the clock, most of the company women would be down in the break room right now, including Robin.  No time like the present!  Getting up from his desk, he headed for the break room.

     Robin chatted animatedly with the other women.  She had been early again for break this morning, just as she had been for every break period all week.  And just like all the others, she would be among the last to go back to her desk.  She noticed Ray walking into the room and immediately remembered the odd conversation she had had with him earlier.  Since she hadn’t heard anything more, she had hoped the subject had been closed and she had tried to put it out of her mind.  But now… now it looked like he was heading straight for her.  She immediately began to worry.

     Ray saw Robin sitting in the middle of the large group of women, all of them chatting like crazy hens!  He was going to single Robin out to talk with her privately again, but he changed his mind.  Chad had been sitting and talking with all the women for the last few months.  Maybe talking to more than just Robin might yield him a few more answers.  Putting his broad “charming” smile on his face, he approached the bunch, immediately catching their attention and ending their various conversations.

      “Good morning ladies,” he said as if he was appreciating the “attributes” of each and every one of them – which he was.  “How are you all this morning?”

      “Hello Ray,” several of them replied.

      “I’m available tonight, if you’re asking,” one of the women added.  “And tomorrow night… and the next… and… whenever you want.”

     Ray smiled directly at her.  “Don’t worry, I’ll remember that.”

     Robin had no doubt that he would. But what did he want?  She was very worried about that.

     Rey turned his gaze around the table to smile at each of them.  “I’m hoping you can all help me with something that has me a bit puzzled,” he told them.

     Robin braced herself.  She had a pretty good idea what he was going to ask about.

     Ray was continuing, “I know now that Chad has been dressing like a woman for the last two months because he lost a bet.”

      “Say what?” one of the women exclaimed.

     Ray looked around him.  It was obvious from the looks on their faces that none of them knew that.  “You didn’t know?” he asked a bit uncertainly.

      “That’s the first I heard it!” one of them replied.

      “Where’d you get that from?” another woman asked.

     Ray was totally befuddled.  “I just… I just… I thought that from what I heard, plus what I’ve seen him doing… that… well…  You mean it’s not because of some bet?”

      “First I’ve heard of it!” one of the women told him rather pointedly.

     In desperation, Ray looked to Robin for confirmation. 

     Robin saw him looking at her, waiting for her to back him up somehow.  But she couldn’t do that… and more importantly, to save her own neck, she’d rather not do that.  She settled for the best she could do under the circumstances.  “Um…  I know Chad made a bet with someone, but as to him dressing like he does because he lost that bet, I never heard about that.

      “But…” Ray started to argue. 

      “I don’t know!” Robin insisted.  “Chad hasn’t told us anything!  He’s really been rather closed mouthed about all of it… since the beginning!”

      “He sure has!” another woman confirmed.  And Ray heard most of them agreeing. 

      “But you work with him!” Ray argued.  “You have to know something.”

      “Like what?” Robin asked.

      “Like how much money was he after in the first place?”

      “Money?”  Robin remembered that it was the one topic he had mentioned the last time he had talked to her about this.  And she still had the same answer.  “What money?”

      “Who told you all this?” someone asked Ray.

      “Derek,” Ray told her.  “He told me all about it.”

      “Then he most not have told you everything if you’re still asking questions.”

      “I was… a bit drunk at the time,” Ray admitted.

      “Then maybe you should ask Derek to fill you in on the rest of it… and then come back and fill us in too!  Because I don’t know anything about it!”  Her sentiments were echoed by many of the women at the table.

     Ray looked around.  Not only had they all been no help, none of them had known anything about the bet at all.  And he was sure Derek had told him it was all because of a bet!  He nodded toward the woman who had spoken last.  “I guess I’ll have to do just that!”  He looked at all the women again.  “Thank you ladies for your…” he would have said help, but they hadn’t helped at all.  “time,” he finally finished.

     Robin watched as he walked away… just as all the other women did.  And then the explosion hit.  And most of that explosion was aimed directly at her.  Question after question, demand after demand – most of which Robin either couldn’t answer… or more often, wouldn’t!  And when the women started to leave to go back to work, Robin was among the very first to leave as well.  Not only did she feel like she had to get out of there, she needed answers now as well. 

     Somehow in the mix of discussions after Ray had left, every one of those women back there was now firmly convinced that Chad… Sissy… was dressing like he did – because he had already lost some big bet!  And worse… they all somehow figured that since she worked with him, she had to know all about it – whether she admitted it or not. 

     What had Derek told Ray?  And more importantly, what the heck was she supposed to tell everyone else?

     Derek’s phone rang as he was helping to pull some wiring through the conduit to rout it where it needed to go.  He was actually supervising, but in a job like this, even a supervisor had to do a lot of the dirty work.  Since he was currently busy, he let the phone keep ringing until it finally went to voicemail.  Only when he had a spare second a few minutes later did he check to see who had called.  Ray!  What the heck did he want now?  He was too busy just then to talk with Ray.  Way too busy!  The fact that he flat out didn’t want to talk to Ray didn’t really matter.

     But two minutes later, his phone rang again.  He was irritated because he really didn’t need to talk with Ray… he was still somewhat angry with Ray.  But when he picked his phone up and saw Robin’s name on the caller id instead, he just knew that there was trouble of some kind.  This time he answered it.  “Hello?”

      “Derek!” Robin exclaimed.  “What the heck did you tell Ray about Sissy?”

     Derek didn’t miss the panic in Robin’s voice.  “A good question,” Derek replied.  “I’m pretty sure I told him absolutely everything, including a few things I’m sure I probably shouldn’t have.  Why?  Is he causing you trouble?”

      “Not the way you think,” Robin told him.  “Somehow he’s convinced that Sissy is dressing like he is because he ‘already’ lost the bet with Mel.  And he has everyone else convinced now of that too.  And they all want me to fill them in on what’s going on!  But I don’t know what you told them… and… there are some things I absolutely don’t dare tell them!”

      “Wait a minute!” Derek said.  “I didn’t tell Ray that Chad had already lost the bet.”

      “Did you tell him about the… incontinence thing?  The main thing their bet is all about?”

      “I’m sure I did,” Derek admitted.  “Why?  What’s he saying about that?”

      “He hasn’t even mentioned it.  It’s more like he doesn’t know about that at all!”

      “Strange,” Derek mused, “I’m sure I told him.  But he was pretty drunk when I said it, so maybe it didn’t register with him.”

      “So what do I tell everyone?” Robin asked.  “Ray’s got everything all confused, and everybody is mad at me now because they think I have all the answers… but I don’t know what to tell anyone!”

      “I don’t know,” Derek replied.  “Maybe you should try to contact Mel and ask her.  That’s my advice.  And in the meantime, don’t say anything to anyone.  Let Mel decide how we should handle this.”

      Chad got out of the car in the mall parking lot.  He slung his heavy diaper bag over his shoulder and put the baby bottle he was currently drinking back in his mouth as Mel had told him to, and followed her toward the main entrance to the mall.  But once they got to the mall entrance, Mel walked off toward the side a bit instead of going in.  “Set your diaper bag down there Sissy,” she told him.  She waited until he had done that.  “Now I’m going to be busy for a few minutes, so I want you to give a nice sissy greeting to everyone who walks past.  I’m sure everyone will be so happy to have you make their day for them.  And when you’re not curtseying for anyone, you can keep that bottle in your mouth.  I’m going to give you every chance I can today for you to earn a little reward time… but you’re still going to have to earn it!”  With that, she walked further away up the sidewalk as she pulled her phone out of her purse. 

     Chad stared after her.  He dreaded these trips to the mall.  Okay, yes, he loved them too – for a different reason.  And today Mel was going out of her way to humiliate him as much as possible.  Was that because the last few days had been so easy?  Or because their bet was almost over?  Not that it mattered, he was still terrified inside.  She had made him do this once before… stand here near an entrance while wearing one of his sissy dresses to “greet” everyone.  The funny thing was though, as completely humiliating as it was, it was still kind of fun.  Acting like a total sissy right in front of everyone… showing everyone how much of a crazy sissy he was.  In fact, it was the best way he could get through it.  The secret was in trying as hard as possible to actually enjoy it… despite how dumb and stupid and idiotic and silly and humiliated he felt.